41570-74-5Relevant academic research and scientific papers
One-pot synthesis of cyclopropane derivatives with a cis : Trans stereoselectivity by Wittig olefination-sulfur ylide cyclopropanation sequence
Huang, Wenhua,Wang, Lai-Ling
, p. 380 - 384 (2013/07/26)
Cyclopropane derivatives were synthesised in one pot from aromatic aldehydes, phenacyltriphenylphosphonium bromide, and S-phenacylthiolanium bromide by a Wittig olefination-sulfur ylide cyclopropanation sequence. When Cs2CO3 was used as the base and CH3CN/water (8:2, v/v) as the solvent, the major product was the cis-1,2-dibenzoyl cyclopropane. In contrast, when using DBU as the base and MeOH as the solvent, the major product was transdibenzoyl cyclopropane. In some cases, the major isomer was obtained in high purity and good yield by simple filtration.
Indium(I) bromide-promoted stereoselective preparation of cyclopropanes via sequential aldol-type coupling/elimination/Michael-induced ring closure reaction from α,α-dichloroacetophenone and aldehydes
Peppe, Clovis,das Chagas, Rafael Pav?o,Burrow, Robert Alan
, p. 3441 - 3445 (2008/12/22)
The indium enolate generated from indium(I) bromide and α,α-dichloroacetophenone reacts with aldehydes to produce (syn + anti)-2-chloro-3-hydroxy-propan-1-ones which can be converted to their trans-prop-2-en-1-ones derivatives upon reaction with an extra equivalent of InBr. The enones undergo Michael-induced ring closure reactions with an extra equivalent of the initial enolate to afford the corresponding cyclopropane derivatives, according to a sequenced reaction mechanism.
